645-00-1

Basic information

• Product Name: 1-Iodo-3-nitrobenzene
• Synonyms: 1-iodo-3-nitro-benzen;3-Nitroiodobenzene;Benzene, 1-iodo-3-nitro-;m-Nitrophenyliodide;3-IODONITROBENZENE;1-IODO-3-NITROBENZENE;M-IODONITROBENZENE;M-NITROIODOBENZENE
• CAS NO: 645-00-1
• Molecular Formula: C₆H₄INO₂
• Molecular Weight: 249.01
• EINECS: 211-427-9
• Product Categories: Benzene derivates;Iodine Compounds;Nitro Compounds;Nitro Compounds;Nitrogen Compounds;Organic Building Blocks
• Mol File: 645-00-1.mol
• Article Data: 88

Chemical Properties

• Melting Point: 36-38 °C(lit.)
• Boiling Point: 280 °C(lit.)
• Flash Point: 161 °F
• Appearance: yellow to yellow-green powder
• Density: 1.9477
• Vapor Pressure: 0.0063mmHg at 25°C
• Refractive Index: 1.663
• Storage Temp.: Refrigerator (+4°C) + Flammables area
• Water Solubility: insoluble
• Sensitive: Light Sensitive
• Stability: Stable. Highly flammable. Incompatible with strong bases, strong oxidizing agents.
• BRN: 1525167
• CAS DataBase Reference: 1-Iodo-3-nitrobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Iodo-3-nitrobenzene(645-00-1)
• EPA Substance Registry System: 1-Iodo-3-nitrobenzene(645-00-1)

Safety Data

• Hazard Codes: Xn,F,Xi
• Statements: 20/21/22-36/37/38-36-33-11
• Safety Statements: 26-36/37/39-45-16-36
• RIDADR: UN 1325 4.1/PG 2
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 4.1
• Hazardous Substances Data: 645-00-1(Hazardous Substances Data)

Usage

Uses

1-Iodo-3-nitrobenzene was used in the synthesis of 5-substituted pyrrolo[3,2-b]pyridine amide and 3′-nitro-4-methylthiobiphenyl. It was used in palladium(0) catalyzed cross-coupling reaction between heteroarylzinc iodide and unsaturated iodide.

Definition

ChEBI: A C-nitro compound that is nitrobenzene bearing an iodine substituent at C-3.

General Description

Monoclinic prisms or tan solid.

Upstream product

• 20691-72-9 4-iodo-2-nitroaniline 
• 69180-54-7 1-iodosyl-3-nitro-benzene 
• 98-95-3 nitrobenzene 
• 139-02-6 sodium phenoxide 
• 23351-89-5 m-nitrodiphenyliodonium bromide 
• 13331-27-6 m-nitrobenzene boronic acid 
• 67-66-3 chloroform 
• 6293-62-5 bis-(3-nitro-phenyl)-iodonium ; chloride 
• 7664-93-9 sulfuric acid 
• 7553-56-2 iodine 
• 591-50-4 iodobenzene 
• 7697-37-2 nitric acid 
• 722-56-5 diphenyliodonium nitrate 
• 126086-78-0 1-dimethyl-chlorostannyl-3-nitrobenzene 

Downstream Products

• 16307-37-2 3-nitro(diacetoxyiodo)benzene 
• 16825-78-8 1-iodoxy-3-nitrobenzene 
• 51264-60-9 3-nitro-2'-methylbiphenyl 
• 23377-21-1 1,2-bis(3-iodophenyl)diazene 
• 958-96-3 3,3'-dinitro-1,1'-biphenyl 
• 952-04-5 3-chloro-3'-nitro-biphenyl 
• 620-55-3 1-nitro-3-phenoxybenzene 
• 88-67-5 2-Iodobenzoic acid 
• 50829-58-8 3-(4-methylphenoxy)nitrobenzene 
• 107622-63-9 1-methoxy-2-(3-nitro-phenoxy)-benzene 
• 116530-27-9 (3-nitro-phenyl)-o-tolyl ether 
• 10304-72-0 3-nitro(dichloroiodo)benzene 
• 51294-43-0 4-iodo-1,2-dinitro-benzene 
• 626-01-7 3-Iodoaniline 

Relevant articles and documents

Synthesis of 4-substituted azopyridine-functionalized Ni(II)-porphyrins as molecular spin switches

We present the synthesis and the spin switching efficiencies of Ni(II)-porphyrins substituted with azopyridines as covalently attached photoswitchable ligands. The molecules are designed in such a way that the azopyridines coordinate to the Ni ion if the azo unit is in cis configuration. For steric reasons no intramolecular coordination is possible if the azopyridine unit adopts the trans configuration. Photoisomerization of the azo unit between cis and trans is achieved upon irradiation with 505 nm (trans→cis) and 435 nm (cis→trans). Concurrently with the isomerization and coordination/decoordination, the spin state of the Ni ion switches between singlet (low-spin) and triplet (high-spin). Previous studies have shown that the spin switching efficiency is strongly dependent on the solvent and on the substituent at the 4-position of the pyridine unit. We now introduced thiol, disulfide, thioethers, nitrile and carboxylic acid groups and investigated their spin switching efficiency.

ipso-Bromination/iodination of arylboronic acids: Poly(4-vinylpyridine)-Br2/I2 complexes as safe and efficient reagents

Poly(4-vinyl pyridine) supported bromine/iodine complexes were prepared and probed for ipso-bromination/iodination of arylboronic acids. These solid complexes with catalytic amount of additive are found to be safe and efficient reagent system for the ipso-bromination/iodination. The reaction occurs under mild conditions and tolerates various functional groups resulting in products with high selectivity and yields.

Rapid Iododeboronation with and without Gold Catalysis: Application to Radiolabelling of Arenes

Radiopharmaceuticals that incorporate radioactive iodine in combination with single-photon emission computed tomography imaging play a key role in nuclear medicine, with applications in drug development and disease diagnosis. Despite this importance, there are relatively few general methods for the incorporation of radioiodine into small molecules. This work reports a rapid air- and moisture-stable ipso-iododeboronation procedure that uses NIS in the non-toxic, green solvent dimethyl carbonate. The fast reaction and mild conditions of the gold-catalysed method led to the development of a highly efficient process for the radiolabelling of arenes, which constitutes the first example of an application of homogenous gold catalysis to selective radiosynthesis. This was exemplified by the efficient synthesis of radiolabelled meta-[125I]iodobenzylguanidine, a radiopharmaceutical that is used for the imaging and therapy of human norepinephrine transporter-expressing tumours.